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Ben Stiller can still vividly recall being in the delivery room when his children were born. As he and his wife, actress Christine Taylor, prepared to welcome their eldest, daughter Ella, in 2002, his excitement was mixed with an overwhelming realization. “It’s like, ‘Wow, what’s inside is going to come out,’ ” he says with a laugh.

As he heard his firstborn’s first cries, Stiller stepped up to perform an important task: cutting the umbilical cord. The big moment, which he repeated with son Quinn in 2005, was marked by the kind of pride and anxiety any new dad would recognize. “You don’t want to screw it up, you know?” he says.

The actor-director plays the title character in 'The Secret Life of Walter Mitty.' (Wilson Webb)

These days Stiller, 48, is awaiting another new arrival—his latest film, The Secret Life of Walter Mitty, which he both stars in and directed. Due out on Christmas, this poignant and gently funny movie reinvents James Thurber’s classic short story of an ordinary man with an extraordinarily active imagination, with Stiller’s Mitty, a photo editor at the folding Life magazine, embarking on a globe-trotting adventure that ultimately trumps anything in his daydreams. It is something of a departure for Stiller, who’s best known for his roles in broadly comic franchises like Meet the Parents and Night at the Museum. “At a certain point, you want to be taking chances,” he says. “That’s when you’re having the most vital experiences.”

See Stiller talk about his amazing time in Iceland shooting Walter Mitty—and learn how you could win your own Icelandic adventure—in this exclusive video below. Enter for a chance to win here!

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On the surface, Stiller, the New York City–raised son of actors Jerry Stiller and Anne Meara, would seem to have little in common with his sheltered everyman character. But he insists that even a guy whose films have grossed more than $2 billion at the box office can relate. “As you get older, you start to see the things you haven’t done, the things you want to do, and you seize the moment more,” he says. Inspired by Mitty’s epic trek, Stiller shares his own life-altering expeditions.

Father, Son, and The Holy Land

My dad and I took a father-son bonding trip to Israel when I was about 16. We got a car and drove across the country. We went to Jerusalem and Masada. I’ve always loved history, so it was great exploring that part of the world.

With his dad, Jerry Stiller, in 2012, many years after their trip to Israel. (Nathaniel S. Butler/NBAE via Getty Images)

I went scuba diving in the Red Sea, and my dad took the resort course to learn how to dive, too. I always give him credit for that because he wasn’t really the scuba diving type. So we ended up diving in the Red Sea together. They also had a Jet Ski by the beach. You’re supposed to start on your stomach and then pull yourself up, but he never pulled himself up; he just went around with his feet dangling off at about 40 miles an hour. He was into it.

I met a girl on that trip and we had a whirlwind romance. Is it blasphemous to say we ended up making out near the Western Wall? It might be. But we did. My dad was pretty supportive of my liking this girl even though it was our trip together, which was cool. I was really into Phil Collins at the time; “In the Air Tonight” will always make me think of her. It was one of those times you don’t ever forget.

The Road to Tipperary

In my mid-20s, I had a relationship that didn’t work out and I was trying to find myself a bit. I asked a guy I knew in New York if I could stay on his couch for a few days. The holidays were coming up and I didn’t know how to spend them because I was so broken up. This guy and I didn’t know each other very well, but we both had Irish relatives, so I said, “Let’s go to Ireland for New Year’s.” And he was game. One of my goals for the week was to get away from my phone and not check my messages—not to know that she hadn’t called.

I wasn’t in a celebratory mood on the plane to Dublin because I was thinking, “Where is she right now? Who’s she with?” But there was an announcement from the pilot, “Happy New Year! It just turned midnight.” This was pre-9/11, and the stewardess said, “You can go check out the cockpit if you want.” I was like an 8-year-old boy, saying, “Really?” I remember the pilot was reading the paper while he was flying the plane; that fills you with confidence.

We landed at about five in the morning, and it was like that U2 song with the lyric “All is quiet on New Year’s Day.” We had this eight-day road trip where we drove through the Wicklow mountains down south, then to Galway and up to Belfast. I learned how to drive on the other side of the road; I think I smashed our side mirror a couple of times.

I looked up the town where my mother’s family was from—O’Meara is the original Irish—which is Toomevara, in Tipperary. We didn’t find anybody I was related to. But we had some beers with the locals, and I felt like I connected with the place.

It was one of those things where we both took a chance—“I’ll go on a trip with this guy”—and to this day, we’re really good friends. When it was over, we flew back and I finally checked my messages. She hadn’t called. But I felt better. I felt like I had taken action and done something for myself. Everybody has stories of times when they’ve tried to figure out their life. You’re stepping into the unknown. In retrospect, you look back and go, “Things happen the way they’re supposed to happen.” But at the time it’s scary. That trip helped me move forward and get more of a sense of myself.

Failure Is an Option

Back in 1996 I directed a movie called The Cable Guy, starring Jim Carrey. It was a great creative experience but the movie was a big flop. I remember I stopped reading the New York Times review after the sentence that said, “But the true disaster movie of the summer may just be The Cable Guy. …” I knew it wasn’t going in a good direction.

Dealing with that made me appreciate what came afterward much more. It also taught me that the outcome doesn’t always relate to the experience you have doing something—and that doesn’t mean it wasn’t valid or good, especially if it was what you wanted to do. The Cable Guy was Jim Carrey at the height of his career saying, “I want to do something that’s not safe.” I always admired that he made that choice and never backed away from it. Luckily I didn’t know that we were going off into an area that could be really tricky.

After that, I sort of waited for the dust to settle. I wrote a script with a friend that never got made, but I delved into that fully and had a great time doing it. And then a couple of years later I was in a movie that did well, There’s Something About Mary, and I knew that if people weren’t calling me as a director, I was fortunate enough to be able to work as an actor. It was good to have the Cable Guy experience before that success; it wasn’t that I just came out of the gate and everything was great, with me thinking this is how it’s going to be all the time. I’ve had all sides of it throughout my career.

Finding The One

I proposed to Christine when I was rehearsing Meet the Parents. I flew from New York to L.A. to surprise her. I put candles and rose petals leading through her house to the back deck, where I was waiting; it was really cheesy and romantic. She sensed when she saw the petals that it was a friendly intruder. I got down on one knee and then realized I had totally forgotten the ring! So I was like, “Hang on a second.” I had to run into the other room and get it out of my backpack. I got back and said, “Will you marry me?” And she said, “Yes, of course!” I was so happy.

I asked her father for permission before I did it. The first time I met her family was when her grandfather passed away, and I went to Pennsylvania. It was like Meet the Parents in real life, because Christine’s father is an intimidating guy who owns a security company; we’re good friends now, but at the time I was in the basement rec room saying, “I really would like to marry your daughter. …” He’s a man of few words but he was very welcoming. I was more nervous asking him than asking her, because I thought that Christine and I felt the same way.

Our relationship was a gradual thing that happened over a quick period of time, maybe seven or eight months. We just started hanging out with each other and it developed into, “Wow, this feels great. I really like this person. I think I love this person. I really do—I love this person!” It hit me out of the blue.

I think marriage, or any relationship, gets interesting about five or six years in. People are always changing and you can’t take things for granted. It’s daunting to think, “This is it—everything’s going to stay the same.” That’s scary. You need to evolve together and listen to each other as you go through ups and downs.

Life throws a lot of things at you; romance comes and goes. Having Christine as my best friend, someone I can share everything with, is huge. We can really lean on each other. She’s very funny, too, and laughter is such an important part of a relationship. Sometimes I’ll get a little intense, and she’s a much lighter person; she’s great at pulling me out of that. She makes me laugh or see how ridiculous I’m being.

Baby on Board

When your wife is pregnant for nine months, you get used to the idea of pregnancy. Obviously, you know where it’s leading, but it almost becomes this abstract idea; and then suddenly the next time you go back to the house, you have another person living with you. Who you’ve just met. Your child.

Watching the New York Knicks play in 2011 with son Quinn, wife Christina, and daughter Ella. (Anthony J. Causi/Splash News)

So I will always remember that drive home in the car with Ella. I was very nervous. We’d been around a lot of people, nurses and doctors, telling us what to do—and now it was just us with the baby. It was my first time with the car seat and I wanted to make sure it was all secured. (Eleven years later, I’m still learning how to work a car seat.) I remember thinking, “Drive really carefully. …” It’s precious cargo! And the huge realization that I was powerless now over the feeling I had for the baby. How much I loved this person and wanted her to be okay.

I was thinking moment to moment: Just get her from the baby carrier to the crib. … It’s a short distance but a huge change. Suddenly the house feels different. Then the journey of watching your kids grow up unfolds. You’re just figuring it out as you go, no matter how many books you’ve read or how many ideas you have of what you want to do. You see the way they look at the world, and that affects how you look at it.

My kids are 11 and 8 now, and I can see aspects of myself in them but I also see two totally unique individuals. And I wonder how they became so well adjusted!

Online Extras From Ben

On directing himself:“Almost every movie I’ve directed and acted in, I’ve looked for somebody else to either direct or act. [Doing both] is frustrating. You can never be in two places at once, and then you’re stuck having to stare at yourself in the editing room for a year, which is probably the worst part of it. [laughs] But when I’m thinking about doing something, I’m thinking, ‘How would I feel about this as an actor if I wasn’t directing it?’ and ‘How would I feel about it as a director if I wasn’t acting in it?’ And if there’s an equal connection, I’ll say, ‘OK, I’ll try it.’ ”

On his daughter, Ella, teasing him:“[The kids] do impressions of me. My daughter really makes fun of me because of how I eat; she thinks I eat way too healthfully, because I don’t have gluten and for a while I was vegan. She gives me a hard time, like, ‘Come on, have some ice cream! Eat a bit of pizza!’ So I say, ‘What will you do if I eat the pizza—will you stop complaining about going to school for a week?’ She’s like, ‘No way!’ [laughs] Sometimes I take a little nibble of pizza just to blow her mind.”

On his experience doing The Ben Stiller Show, which ran for only one season, in 1992-3, but won an Emmy:“We had no idea what we were doing in terms of making a show. There wasn’t any science going into it, with us thinking, ‘How do we make this appeal to viewers?’ And I think that’s a good thing. It wasn’t like we were trying to figure out a show that would be a hit. And it wasn’t. [laughs] It was just us doing what we thought was funny and good. I think there’s a purity to that which is great. We were lucky to get the opportunity.

“I wasn’t bummed when it got cancelled, because we’d been through such a process getting it on the air, and the doing of it was so much work. By the end of six months we were all looking at each other like, ‘How are we gonna keep doing this?’ Right off the bat, when [the ratings weren’t good], we saw the writing on the wall.”

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